187035-79-6

Basic information

• Product Name: ETHYL 2-CHLORO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• Synonyms: ETHYL 2-CHLORO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE;Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-;5-Pyrimidinecarboxylic acid, 2-chloro-4-(trifluoromethyl)-, ethyl ester;Ethyl 2-chloro-4-(trifluoromethyl)pyrimidne-5-carboxylate ,97%;2-Chloro-4-(trifluoromethyl)pyrimidine-5-carboxylic acid ethyl ester;Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate ,97%;Ethyl 2-chloro-4-(trifluoromethyl)pyrimidne-5-carboxylate;2-Chloro-5-(ethoxycarbonyl)-4-(trifluoromethyl)pyrimidine
• CAS NO: 187035-79-6
• Molecular Formula: C₈H₆ClF₃N₂O₂
• Molecular Weight: 254.59
• Product Categories: API intermediates;Esters;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Pyrimidine
• Mol File: 187035-79-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 336.18 °C at 760 mmHg
• Flash Point: 157.116 °C
• Appearance: liquid
• Density: 1.449 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.466
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -5.61±0.29(Predicted)
• CAS DataBase Reference: ETHYL 2-CHLORO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-CHLORO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE(187035-79-6)
• EPA Substance Registry System: ETHYL 2-CHLORO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE(187035-79-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 187035-79-6(Hazardous Substances Data)

Usage

Chemical Properties

liquid

Uses

Intermediate for life science products. Attributes For further information please contact us Contact

InChI:InChI=1/C8H6ClF3N2O2/c1-2-16-6(15)4-3-13-7(9)14-5(4)8(10,11)12/h3H,2H2,1H3

Upstream product

• 571-55-1 ethyl 2-(ethoxymethylidene)-4,4,4-trifluoro-3-oxobutanoate 
• 2924-80-3 ethyl 4,4,4-trifluoro-3-oxo-2-(ureidomethylidene)butanoate 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 154934-97-1 ethyl 2-hydroxy-4-trifluoromethylpyrimidine-5-carboxylate 

Downstream Products

• 851508-34-4 2-(4-trifluoromethoxy-phenyl)-4-trifluoromethyl-pyrimidine-5-carboxylic acid ethyl ester 
• 1453841-32-1 ethyl 4-(trifluoromethyl)-2-(1-trityl-1H-pyrazol-4-yl)pyrimidine-5-carboxylate 
• 1221785-58-5 ethyl 2-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoromethyl)pyrimidine-5-carboxylate 
• 154934-99-3 2-chloro-4-(trifluoromethyl)pyrimidine-5-carbonyl chloride 

Relevant articles and documents

PROCESS FOR THE PRODUCTION OF PYRIMIDINE-5-CARBOXYLATES

Pyrimidine-5-carboxylates of formula wherein R is C1-4 alkyl, R1 is C1_4 alkyl or trifluoromethyl, R2 is hydrogen or C1 alkyl and X is hydroxy, chlorine or bromine, are prepared from 3-oxoalkanoates of formula with urea and orthoesters of formula R2C(OR)3 (III). The intermediate 2-acyl-3-ureidoacrylate, without being isolated, is reacted to give a 2-hydroxypyrimidine-5-carboxylate [(I), X = OH] or a hydrate thereof, which is optionally converted into the corresponding chloro or bromo compound (I, X = Cl, Br).

Inhibitors of NF-kappaB and AP-1 gene expression: SAR studies on the pyrimidine portion of 2-chloro-4-trifluoromethylpyrimidine-5-[N-(3', 5'-bis(trifluoromethyl)phenyl)carboxamide].

We investigated the structure-activity relationship studies of N-[3, 5-bis(trifluoromethyl)phenyl][2-chloro-4-(trifluoromethyl)pyrimidin-5 -yl]carboxamide (1), an inhibitor of transcription mediated by both NF-kappaB and AP-1 transcription factors, with the goal of improving its potential oral bioavailability. Compounds were examined for cell-based activity, were fit to Lipinski's rule of 5, and were examined for potential gastrointestinal permeability using the intestinal epithelial cell line, Caco-2. Selected groups were substituted at the 2-, 4-, and 5-positions of the pyrimidine ring using solution-phase combinatorial methodology. The introduction of a fluorine in the place of 2-chlorine of 1 resulted in a compound with comparable activity. However, other substitutions at the 2-position resulted in a loss of activity. The trifluoromethyl group at the 4-position could be replaced with a methyl, ethyl, chlorine, or phenyl without a substantial loss of activity. The carboxamide group at the 5-position is critical for activity. If it was moved to the 6-position, the activity was lost. The 2-methyl analogue of 1 (81) showed comparable in vitro activity and improved Caco-2 permeability compared to 1.